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Updated: May 31, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
2,4,6-Trinitro-N-[4-(phenyl-diazen-yl)phen-yl]aniline
1Faculty of Science and Technology, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia.
Researchers synthesized a novel compound, C(18)H(12)N(6)O(6), from aniline yellow and picryl-sulfonic acid. Structural analysis revealed specific dihedral angles and an intramolecular hydrogen bond, offering insights into molecular geometry.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Aniline yellow is a known azo dye.
- Picryl-sulfonic acid is a strong organic acid.
- Understanding molecular interactions is crucial in chemistry.
Purpose of the Study:
- To synthesize and characterize a new compound formed from aniline yellow and picryl-sulfonic acid.
- To determine the molecular structure and conformation of the synthesized compound.
- To investigate the presence of intramolecular hydrogen bonding.
Main Methods:
- Chemical synthesis via reaction of 4-(phenyl-diazen-yl)aniline with picryl-sulfonic acid.
- Single-crystal X-ray diffraction for structural determination.
- Analysis of dihedral angles and hydrogen bonding interactions.
Main Results:
- The compound C(18)H(12)N(6)O(6) was successfully synthesized.
- The dihedral angle within the diphenyl-diazenyl moiety is 6.55°.
- The dihedral angle within the picrate-aniline moiety is 48.76°, and an intramolecular N-H⋯O hydrogen bond was identified.
Conclusions:
- The synthesis yielded a novel compound with a defined molecular structure.
- The observed dihedral angles indicate specific conformational preferences.
- The intramolecular hydrogen bond plays a role in the molecule's stability and conformation.
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